


Sweet Dreams Are Made of This

by WinterWolf610



Category: Supernatural
Genre: Anal Fingering, Blood Play, Bondage, Bottom Dean, Bottom Dean Winchester, Cock Ring, Dom/sub Undertones, Double Anal Penetration, Double Penetration, Foursome - M/M/M/M, Handcuffs, M/M, Mild Hurt/Comfort, Multi, Multiple Orgasms, Oral Sex, Rough Oral Sex, Rough Sex, Sex Machine, Sex Swing, Sex Toys, Size Kink, Top Benny, Top Castiel, Top Crowley
Language: English
Status: Completed
Published: 2014-08-08
Updated: 2014-08-08
Packaged: 2018-02-11 07:33:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,102
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2059422
Author URL: https://archiveofourown.org/users/WinterWolf610/pseuds/WinterWolf610
Summary: <blockquote class="userstuff">
              <p>Dean doesn't know how he got here but he isn't complaining. An angel, a demon and a vampire are all taking care of him. The sex with all three together and with each individually is beyond amazing but when the high starts to fade, Dean realizes that things may not be quite what they seem...</p>
            </blockquote>





	Sweet Dreams Are Made of This

Dean Winchester has never felt like this before. He can barely remember his own name, let alone how he got here. All he knows is that his body has become a battleground. An angel, a demon and a vampire are all battling for dominance over him.

Although at the moment, it seems like none of them are losing. They're all trying to outdo the others. They're precariously draped over the foot of the bed, with Cas under him, Crowley behind him and Benny before him. Dean realizes he's feeling fuller than he ever has. He's quite sure he's never been with a man in his life. And at the moment, he's with three. And not just any three. Castiel, Crowley and Benny, no less. He can barely believe it. And they were all naked. More than naked actually. 

They were having sex. A depraved orgy. A porn-worthy foursome. A ménage a... what's the French word for four? _Holy crap_ Dean thinks. Dean's on his hands and knees. Benny's monster cock is thrusting roughly down his surprisingly loose throat. Benny's hand is on his jaw, keeping him from adjusting. Dean thinks that if he did try to adjust, he'd just end up choking. It's hard enough to breathe as it is. Benny's head is thrown back in rapture. Dean also realizes that he's handcuffed and on top of Cas, who's got his hands on Dean's shoulders and his dick pumping away in Dean's gaping ass. Dean's handcuffed hands rest on either side of Cas's neck with the chain behind his head as Dean tries to find purchase. Behind him, Crowley holds his hips bruisingly as he thrusts in opposition to Cas's movements. 

Dean is overwhelmed by the sensations of being fuller than he's ever been and of two dicks alternatively pumping in and out of his over-stretched ass. Dean thinks the liquid he feels in the vicinity is lube. The sensations are perhaps too much. He's too full. Too stretched. Too sensitive. Too overwhelmed. Too close to coming himself. Belatedly, Dean realized that the reason why he hasn't already is because he's wearing a cockring. 

The realization makes him groan around Benny's cock. Benny growls, low and feral. The others pick up on that primal sound and pick up the pace. Dean didn't even realize that was possible. He isn't going to be able to walk tomorrow, he knows. The bed at least is soft on his knees and Cas is somehow giving him a look that is both lustful and sympathetic. That does nothing to slow the angel's assault on his hole however.

Crowley tightens his grip on Dean's hips and leans forward to kiss Dean's neck. He bites gently, but it still draws blood. He laps it up and grins up at Benny. The vampire's rhythm falters for a moment and he growls at the demon. The demon moves to kiss the vampire and share the prize. Benny returns the kiss passionately. Dean groans at the sight and suddenly Benny has thrust all the way down, holding Dean's head in place. Dean can barely swallow the load but he has no choice.

Come dribbles down the corners of his mouth as Benny finally releases him. Cas kisses him and licks up all the come dribbling down his face. Dean can't believe how hot he finds it. With Benny spent, Crowley and Castiel battle within him and Dean's brain has ceased to function other than to utter one hoarse word: "please". He sounds absolutely wrecked because he is. It seems to have affected all three of his partners. A worn-out Benny reenters Dean's vision. 

"Please what, sweetheart?" He drawls. Dean's too far gone to protest the nickname or think any further than his own release. His cock is full to bursting and so close it's painful. All he wants, all he thinks about and all he cares about is release. 

"Please," he begs, "please release me. Please let me come. Please, oh please, please take it off. Please, I'll do anything!" Dean Winchester is the best hunter in America. He likes fast cars, greasy burgers and frisky women. He does not beg. He especially does not beg other men to let him come but he's been reduced to a whimpering mess by the attentions of his three male lovers. Furthermore, he's promised anything in exchange. 

The three supernatural beings are aware of and savor this momentous occasion. The former crossroads demon leans forward to whisper in his ear, "Anything, kitten? Ooh you do know that's a raw deal for you. You're going to get screwed." But he pulled Dean's lips to his with one hand and releases his cock with the other hand. Dean splatters all over Cas's torso. Crowley and Cas's rhythms falter as they ride Dean's ass to completion. Dean falls forward onto Cas and the two dicks fall out of his abused hole. He struggles to catch his breath as his lovers maneuver him onto his back. His wrists are freed and he feels hands massaging circulation gently back in. A soft, warm cloth cleans up his face, torso and hole. Soft kisses all over his skin are the last thing he's aware of as he finally gives into the exhaustion that inevitably follows such a vigorous session of lovemaking. 

•••

When Dean wakes the next morning, he feels content. In fact, he feels happier than he has ever felt. He feels surprisingly rested but when he moves to stretch, he finds that he can't. His hands and feet are chained to the bedposts. It's a different bed than he fell asleep in, he realizes. As he looks around the room, he sucks in a breath. The only thing this room could be described as is a sex dungeon.

All manner of sex toys are mounted all along the wall. Gags and other restraints litter the room as well. There's a sex swing in one corner, and a pole in another. In the other corners, there's some kind of bondage device and a covered something that Dean gets the suspicion is a fucking machine. There doesn't seem to be any whips, floggers, paddles or anything else lying around, to Dean's relief. 

His relief is short lived, however, when Crowley saunters in. "Morning squirrel," he says cheerfully, "How are you feeling today? Not sore I hope. Our dear angel used his mojo to heal you. While that probably means you can walk today, you aren't going to. And worse yet, it undid all that glorious stretching we did to you. Your newly virgin ass is going to have to accommodate me. And as you know, I'm not small."

"You sold your soul for three more inches." The words are out of Dean's mouth before he can process them. His eyes are bugging out from what he can remember from yesterday. Crowley felt larger than average and Dean hadn't even seen what the demon was packing. He couldn't remember quite how he'd ended up with the demon and the angel both inside him with his lips stretched around the vampires long, thick cock. Dean could barely wrap his lips around that monster but he was under the impression that Crowley was probably just as big. He gulped audibly. 

Crowley chuckled at that. "Remember, you do owe us 'anything' for giving you your release and I did promise you were going to get screwed. I promise to make it good for the both of us." With a snap of Crowley's fingers, Dean finds himself gagged. The demon begins to get naked and Dean finally gets a good look at his cock. It's almost as thick as Benny's and probably longer. If Dean didn't already know he could do it, he would have doubted that it would fit inside him. 

Dean isn't quite sure where this desire comes from but he wants Crowley in him as soon as possible. He spreads his legs invitingly, exposing his tight hole to the demon's hungry gaze. Crowley moans at the sight, grabbing the first bottle of lube he can reach and squirts it all over Dean's hole. He recoils from the cold impact but Crowley's hands are all over him, rubbing the lube all over his skin. He bucks impatiently, begging silently to have something breach him and touch him intimately. He longs for the demon to stroke that tiny bundle of nerves inside him. He wasn't sure how he knew that that was going to feel good, but he did. 

He whined around the gag when the demon kept teasing him. He pressed a surprisingly gentle kiss to Dean's pucker as he strode around the room to search for a toy. He came back with a long, thin vibrator. It was thicker than a finger and Dean clenched reflexively. The demon only grinned. He began to lube up the vibrator as he finally breached Dean with a finger. Dean moaned appreciatively as Crowley felt around. He was a bit rough but Dean could take it. Once the demon found his prostate though, the hunter lost all forms of coherent thought. Before Dean realized it, the finger was replaced by the vibrator. Crowley held it to Dean's prostate and Dean tried to squirm away from the intense sensation but his restraints held him. He came so hard his vision whited out for a moment. 

Crowley snickered as he pulled out the vibrator and licked the mess up, taking special pleasure in Dean's increased sensitivity. Dean lays back relaxed until he hears Crowley laughing at him. "Oh squirrel, that was only round one." Dean's eyes widen almost comically as Crowley resumes stretching him. His body is more relaxed but his mind is racing. Crowley's fully hard now so it's likely the demon will take him soon but Dean doesn't know if he can take such a huge cock up his ass after already having come himself. He was already so sensitive. 

That was probably Crowley's purpose, Dean realized belatedly. He probably figured that Dean would panic, so relaxing him first was a good idea. Even still, Dean couldn't help but worry. Crowley began to increase his ministrations and kiss Dean's throat. His other hand ran worshipfully over Dean's body and Dean relaxed into the touches. After a while, Dean closed his eyes and just let Crowley have his way with him. By the time he had four fingers buried in his hole, he was fully ready to take on the demon. 

As Crowley sheathed himself to the hilt within Dean, the hunter felt the air being pushed out of his lungs. As much as the demon prepared him, it still wasn't enough. It was agonizingly slow as he was being filled up and stretched even further. The burn was so familiar by now that he was beginning to feel immune to it. When he finally bottomed out, both parties let out the breaths they'd been holding. When Dean felt adjusted, he signaled to Crowley to get moving. He began to slowly pick up the pace until he was positively slamming into Dean. He was sure he was going to be bruised from Crowley's balls slapping against him. Dean moaned at the thought and shifted to give Crowley as much more access as he could, given his restraints. Crowley slammed into him with supernatural strength and soon both were coming, panting loudly and utterly spent.

The King of Hell pressed a tender kiss to the hollow of the hunter's throat. He cleaned the man's torso tenderly and unbound his arms and legs. With a touch, the circulation returned. Demon sex powers Dean assumed. He led Dean to the sex swing in the corner and strapped him into it, leaving him off the ground and his hole exposed. Crowley then dressed himself and disappeared with a snap. He'd left Dean's hole sloppy but plugged. Dean assumed the anal plug meant he wasn't going to be alone for long.

•••

It was only a moment before Dean discovered that he wasn't wrong. Benny barged in, bare as the day he was born. Seeing the state Dean was in drew a lusty moan from the vampire. "Oh Dean, if only you could see how delicious you look, brother. All tempting and open and ready. I bet you want my cock. Your greedy little hole needs to be filled, doesn't it? One cock just isn't enough for you, is it, hmm sweetheart?" Dean moans wantonly as Benny lubes up his huge cock. Dean's sure it's the biggest of the three and he wants it in him right now. 

"Oh you take it so well," Benny drawls as he penetrates Dean. Dean can't suppress the noises that he's making as Benny doesn't even stop to let Dean adjust before he's setting a brutal pace and using the swing to move Dean to meet his every thrust. Benny feels impossibly deep inside him and he keeps saying the filthiest things. 

"No one takes cock as good as you, Winchester. Feel so good. I never want to pull out. Just want to pound into you all the time. You make such pretty noises. Makes me wild for you. Just want to get so deep inside you that you always feel me. You love my big dick don't you, boy? You love having your ass split and stuffed. You never knew you could have something so big up inside you, did you? But now that you do, you can't go without it. You want this big cock so badly. I'm going to give it to you so good. I'm going to make you scream yourself hoarse around that gag. You're going to come so hard you see stars. And when you're done, I'll fuck you again. By the end, you'll forget your name. You won't know anything but how good I fucked you." 

Benny makes good on all his promises. The hunter can't remember anything else other than how good it feels to have a huge cock up his ass. He can't even recall how he ended up back on the bed, untied and ungagged but too exhausted to move away from the merciless fucking machine that was pounding into his hole now that Benny's left him. Dean's lost track of how many times he's come but all he can focus on is the next robot piston into his now gaping hole. Benny certainly fucked him loose and this oversized mechanical dildo isn't helping any. Dean can only whimper and close his eyes as the next thrust inevitably comes. 

•••

When it finally stops, Dean is shaking. He doesn't even open his eyes as firm but gentle hands move him further up the bed and clean him off, murmuring into his ear sweet nothings in a gravelly voice. He reaches out for Cas and wraps him tightly in his arms. He opens his eyes as he kisses the angel's lips, cutting off whatever he was going to say. As they pull apart, Castiel asks, "Dean, are you alright?"

"Fine. I'm fine. I can't remember how I got here but hot damn I never thought I'd get fucked _this_ way by three supernatural beings." Dean flashes Cas his most reassuring grin to cover for his raspy, fucked out voice. "I'm ready for round three if you are, Cas." Dean finds himself promptly spread apart and split open in response. Cas's eyes never leave Dean's as he begins a steady pace. His actions are deliberate and intense and Dean can't help but give Cas such a look of both lust and affection. 

Cas, however, looks grimly determined as he fucks hard into Dean. "I'm not sure how I got here either," he says conversationally as he begins to play with Dean's sensitively nipples. 

"What?" Dean gasps between moans. 

Cas begins to rapidly jerk Dean off before he continues. "We were hunting a djinn with Sam before this. I do believe we are in a drug-induced dream." The hunter has the most incredulous expression on his face. 

"What the fuck, Cas?" Dean practically yells, "You tell me we're in some freaky sex dream and yet you still fuck me? What the hell man?! Friends don't fuck each other, dream or not!" Tired as he is though, he can't even move. 

"You didn't protest me or any of the others before I told you this was a dream," Cas says. He stops his motions, but doesn't pull out.

"That's not the same, Cas," Dean huffs. 

"I don't see how. If-" Cas's words are cut off as Dean finds himself suddenly thrown back into the real world. He's in bad shape. His head throbs and he's handcuffed and suspended from a hook. A sore spot in the crook of his elbow tells him that he just had the IV ripped out. He blinks the blood out of his eyes and catches a glimpse of Sammy fighting off the djinn. As he looks around, he sees Cas in a similar state to himself. He tries to shout for Sammy but his voice is too hoarse.

Thankfully, the djinn proves no match for the younger Winchester and soon Dean and Cas are freed. The rest passes as a blur until Dean and Cas are sitting across from each other at a crappy motel table while Sam goes to buy more supplies and food. After their ordeal, Sam was reluctant to leave them alone but had little choice. Besides, Dean and Cas had some things to work out. Dean quickly realized his voice was still hoarse and his ass was definitely sore, dream or not. Which means Cas had been in the middle of fucking him when they'd been rescued. 

"Cas, I-" Dean began but he was cut off by Castiel. The angel looked stern so Dean shut up and listened. 

"Dean I wanted to apologize to you for what I did during the shared djinn dream. I don't wish for my actions to jeopardize our friendship but I-"

It was Dean's turn to cut him off this time. "Cas, I'm the one who should be apologizing. I was just kind of freaked out. Honestly... It was a bit shocking but... I never knew it could feel that good." Dean flushed crimson at that. Cas was staring unblinkingly at him, eyes squinted and head cocked to the side. Dean averted his gaze in shame. 

"You found my penetration of you pleasurable?" the angel asked. 

"Well, um, yes," Dean replied sheepishly. He tentatively looked up to meet Cas's gaze. To his surprise, the look he receives in return is positively predatory. 

"Well then. Let's finish what we started."


End file.
